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Сonformational study of persulfated propyl glucuronide
Alexey G Gerbst1, Dmitry Z Vinnitsky1, Andrey S Dmitrenok1
1Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Carbohydrate Research
|November 28, 2017
Summary
Persulfated glucuronic acid exhibits unique NMR spectral properties. Conformational analysis reveals skew-boat forms, not a simple chair inversion, dominate its structure.
Area of Science:
- Carbohydrate Chemistry
- Structural Biology
- Biophysical Chemistry
Background:
- Glucuronic acid is a key component of glycosaminoglycans, existing in various sulfated forms.
- Previous studies suggested unusual NMR data for persulfated glucuronic acid might indicate a complete chair conformation inversion.
Purpose of the Study:
- To conduct a detailed conformational investigation of persulfated glucuronic acid.
- To clarify the structural distortions observed in NMR spectra.
Main Methods:
- Nuclear Magnetic Resonance (NMR) spectroscopy, specifically analyzing 1H-1H coupling constants and chemical shifts.
- Experimental Nuclear Overhauser Effect (NOE) data analysis.
- Computational conformational analysis.
Main Results:
- The pyranoside ring distortion in persulfated glucuronic acid is more complex than a simple 4C1↔1C4 inversion.
- Experimental NOE data strongly support the presence of two skew-boat conformers, OS2 and 3S1.
- These skew-boat conformers significantly contribute to the overall conformational equilibrium.
Conclusions:
- The conformational behavior of persulfated glucuronic acid is accurately described by a combination of skew-boat conformers.
- This finding refines our understanding of glycosaminoglycan structural dynamics and NMR spectral interpretation.
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